反应详情

温度

100 °C

A solution of 4-(4-bromophenyl)-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (0.256 mmol) in dioxane (1.5 mL) was treated with the HCl salt of N,N-dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine (0.281 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane adduct (10 mg), and 2M aq potassium carbonate (0.767 mmol). The reaction mixture was purged with nitrogen, sealed, and stirred at 100° C. overnight. The reaction mixture was cooled to room temperature and was diluted with water (50 mL). The aqueous layer was acidified to pH˜4 using 1N aq HCl and was extracted with dichloromethane. The organic layer was dried over magnesium sulfate, treated with Si-Thiol (Silicycle, 20 mg), filtered, and concentrated in vacuo. The crude residue was purified by reverse phase HPLC (20-50% acetonitrile/water+0.1% NH4OH) to afford the title compound as a beige amorphous solid (28%). MS(ES)+ m/e 446.3 [M+H]+.

1. customThe reaction mixture was purged with nitrogen
2. customsealed
3. temperatureThe reaction mixture was cooled to room temperature
4. additionwas diluted with water (50 mL)
5. extractionwas extracted with dichloromethane
6. dry with materialThe organic layer was dried over magnesium sulfate
7. additiontreated with Si-Thiol (Silicycle, 20 mg)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude residue was purified by reverse phase HPLC (20-50% acetonitrile/water+0.1% NH4OH)